Aircraft hijacking incidents between the United States and Cuba were at their height between 1968 and 1972. These incidents have variously been attributed to terrorism, extortion, flight for political asylum, mental illness, and transportation between the two countries as a result of the ongoing antagonistic Cuba-United States relations and the Communist government restrictions against Cubans attempting to leave Cuba.Testing a rational choice model of airline hijackings Study of data Subsequent measures by both governments contributed to a gradual reduction of reported incidents towards the mid-1970s. Governmental measures included an amendment to Cuban law which made hijacking a crime in 1970, the introduction of metal detectors in U.S. airports in 1973, and a joint agreement between the U.S. and Cuba signed in Sweden to return or prosecute hijackers.

Below is a non-comprehensive list of hijacking incidents of aircraft between Cuba and the United States.

1950s Before the Cuban Revolution: April 9, 1958 A Douglas DC-3, (CU-T266) piloted by Capt. Armando Piedra, co-piloted by Ramon J. Vazquez (el Niño) Cubana de Aviación is hijacked en route from José Martí International Airport, Havana to Santa Clara Airport. The aircraft landed at Mérida-Rejón Airport, Mexico where the hijack ended. This is considered the first hijacking to take place in the Western Hemisphere. April 12, 1958 The crew of a Cuban Airlines DC-3 with 12 passengers on board, diverted their flight from Havana to Santa Clara in Central Cuba, and flew, instead, to Miami, Florida. One of the passengers, United Press reporter Harold Lidin, said that the decision to defect was apparently made after takeoff.United Press, "Plane Commandeered, Flown Out of Cuba", The Washington Post and Times-Herald, Washington, D.C., Monday April 14, 1958, Volume 81, Number 130, page A5 April 13, 1958 A Cuban Airlines DC-3 is hijacked by three crew members, forcing it to fly to Miami. November 1, 1958 A Cubana de Aviación Flight 495, a Vickers Viscount, en route from Miami to Varadero to Havana is hijacked by Cuban militants. The hijackers were trying to land at Sierra Cristal in Eastern Cuba to deliver weapons to Fidel Castro's rebels. As night approached, the plane ran out of fuel and tried an emergency landing at the Preston sugar mill. It did not make it and instead landed in the ocean and broke apart, killing most passengers and crew. There were 6 survivors and 14 dead.

After the Cuban Revolution: April 15, 1959 A plane is hijacked from Cuba to Miami. The hijackers were four members of Batista's Army (three were from the SIM—the Military Intelligence—and one was an aviation mechanic). The airplane is returned by the U.S. April 16, 1959 An Aerovías Cubanas Internacionales C-46 is forced to land in the United States by four men with guns. April 25, 1959 A Cubana de Aviación Vickers Viscount is taken by four hijackers and diverted to Key West, Florida. October 2, 1959 a Viscount of Cubana de Aviación is hijacked on a flight from Havana to Antonio Maceo Airport, Santiago. The aircraft landed at Miami International Airport.

1960s April 12, 1960 A Cubana Vickers Viscount is hijacked by three crew members and a passenger and diverted to Miami. After landing, the hijackers demanded political asylum in the United States. July 5, 1960 A Cubana Bristol Britannia 138 is seized by two co-pilots and diverted to Miami. July 28, 1960 The captain of a Cubana DC-3 and two passengers forced the copilot out of the cockpit. The captain diverted the plane to Miami and requested political asylum. October 29, 1960 Cubana Flight 905, a DC-3, is hijacked by the co-pilot who took an air marshal hostage and forced the plane to fly to Key West. A shooting killed the marshal. The co-pilot and eight passengers involved in the hijack request asylum in the United States; two other passengers also request asylum. December 8, 1960 A Cubana aircraft crashed near Cienfuegos after five Cubans attempted to hijack the plane to the United States. A gun battle killed one person before the flight crashed. January 1, 1961 A Cubana Bristol Britannia 318 is hijacked by two people and diverted to New York City. May 1, 1961 Antulio Ramirez Ortiz hijacks National Airlines Flight 337, a Convair 440, from Miami International Airport to Cuba. July 3, 1961 A Cubana DC-3 is hijacked by 14 people and diverted to Miami. July 24, 1961 Eastern Air Lines Flight 202, a Lockheed L-188 Electra, is hijacked to Cuba. July 31, 1961 Pacific Air Lines Flight 327, a DC-3, is hijacked by Bruce Britt Sr., demanding to be taken to Cuba. The pilot and a ticket agent were both shot by the hijacker, who was overpowered by the copilot and three passengers while the plane was on the ground. August 3, 1961 Continental Air Lines Flight 54, a Boeing 707, is unsuccessfully hijacked to Cuba. President John F. Kennedy orders that the tires be shot out while the plane is on the ground in El Paso. The plane is later destroyed in a suicide bombing the next year. August 9, 1961 Pan Am Flight 501, a DC-8, is hijacked to Cuba. On the same day, a Cubana C-46 experienced an attempted hijacking by 5 Cubans. Two guards on the plane tried to stop the hijacking. A gun battle killed the captain, a hijacker and one guard. The plane made an emergency landing in a sugar cane field. The remaining four hijackers fled the scene. October 26, 1965 National Airlines Flight 209, a Lockheed L-188 Electra, is hijacked by a Cuban with a pellet gun. Wanting to rescue his family in Havana, he is taken down by the crew with a fire axe. November 17, 1965 National Airlines Flight 30, a DC-8, experiences an attempted hijack by a 16-year-old boy armed with a gun demanding to be taken to Cuba. He fired six shots through the floor before being overpowered by a passenger. March 27, 1966 Angel María Betancourt Cueto, armed with a pistol, tries to hijack a Cubana Ilyushin Il-18 (CU-T831) from Santiago de Cuba to Havana, with 97 persons, in an attempt to reach the U.S. The pilot, Fernando Álvarez Pérez, opposed the hijacking and landed in Havana. The hijacker then killed Álvarez and armed guard Edor Reyes, seriously wounding the copilot Evans Rosales. The event had a large effect on Cubans. The hijacker later was caught and executed. November 20, 1967 Louis Gabor Babler, born in Hungary, successfully hijacks a Crescent Airline Piper Apache from Hollywood, Florida to Cuba; the plane was scheduled to go to the Bahamas.

1968 February 17 Thomas J. Boynton hijacks a private charter Piper Apache from Marathon, Florida to Cuba. He returned to the United States via Canada on November 1, 1969, and was sentenced to 20 years for kidnapping. February 21 Lawrence Rhodes hijacked Delta Air Lines Flight 843, a DC-8, from Tampa, Florida to Cuba with 108 other crew and passengers aboard, including golfer Barbara Romack. Cuban authorities provided the passengers with lemonade, coffee, cigarettes, and pictures of Che Guevara and the plane was released after three hours. Rhodes surrendered in Spain on February 10, 1970. A January 4, 1971 hijacking charge against him is dismissed; he was committed to a mental institution; on July 8, 1971, he returns to prison; he is sentenced to 25 years for robbery on July 17, 1972. March 5 Three people hijacked an Avianca C-54 (HK-136) and diverted to Santiago, Cuba. March 12 Three Cubans hijack National Airlines Flight 28, a DC-8 from Tampa, Florida to Cuba; all are fugitives. March 21 An Avensa Convair 440 is hijacked to Cuba by three passengers. June 19 A VIASA DC-9 from Miami is hijacked 15 minutes after takeoff from Santo Domingo and diverted to Santiago, Cuba. June 29 Southeast Airlines Flight 101 is hijacked by one person and diverted to Cuba. July 1 Velasquez Fonseca, born in Cuba, hijacks Northwest Orient Airlines Flight 714, a Boeing 727, from Chicago to Cuba. July 12 Leonard Bendicks hijacks a Cessna 210 from Key West, Florida, to Cuba. He is deported to the U.S. in September 1968. On March 4, 1971, he is sentenced to 10 years for kidnapping. July 17 Hernandez Leyva, a Cuban, hijacks National Airlines Flight 1064, a DC-8, from Los Angeles to Cuba. August 4 Jessie Willis hijacks a Cessna 182 from Naples, Florida to Cuba; he returns voluntarily via Mexico on January 10, 1969; he is sentenced to 10 years for kidnapping; he is paroled on July 28, 1971. August 22 Bill McBride hijacks a Cessna 336 from Nassau to Cuba. September 20 Eastern Air Lines Flight 950, a Boeing 720, is hijacked to Cuba. October 6 A Mexican-owned Hawker Siddeley HS 748 is hijacked by three passengers to Cuba. October 23 Alben Truitt, the grandson of former U.S. Vice President Alben Barkley, hijacks a Cessna 177 from Key West to Cuba; he returns via Canada in February 1969; he is sentenced to 20 years for aircraft piracy and 20 years for kidnapping (to run consecutively). November 4 Raymond Johnson hijacks National Airlines Flight 186, a Boeing 727, from New Orleans to Cuba. November 23 Five Cubans hijack a Boeing 727 from Chicago to Cuba. November 24 Three Cubans hijack a Boeing 707 from New York to Cuba. November 30 Montesino Sanchez, a Cuban, hijacks a Boeing 720 from Miami to Cuba. December 5 Eduardo Castera hijacks a Boeing 727 from Tampa to Cuba. December 11 Two men hijack a DC-8 from St. Louis to Cuba.

1969 January 2, 1969 Two Americans, a man and woman, hijack a DC-8 from New York to Cuba. The hijackers, Tyrone Ellington Austin and Linda Joyce Austin, eventually returned to the US. Tyrone Ellington was killed during an altercation with police in 1971, and Linda Joyce was arrested in 1988 and spent 6 months in prison after it was discovered that she participated in the hijacking. January 9 Ronald Bohle, a 21-year-old Purdue University student, hijacks a Boeing 727 from Miami to Cuba; he returns via Canada on November 1, 1969, and is sentenced to 20 years for air piracy on July 6, 1972. January 11 A man hijacks a 727 from Jacksonville, Florida to Cuba; he returns via Canada on May 5, 1969; he is acquitted of air piracy and kidnapping on grounds of temporary insanity. January 13 A man unsuccessfully attempts to hijack a Convair 880 from Detroit to Cuba; he is sentenced on July 31, 1969, to 15 years for interference with a flight crew; he had a history of mental illness. January 17 A man from the Dominican Republic hijacks a DC-8 from New York to Cuba. January 24, 1969 A man hijacks a Boeing 727 from Key West to Cuba; he was a 19-year-old Navy deserter who "didn't want to go to Vietnam". January 28 Two men successfully hijack a DC-8 from Los Angeles to Cuba; they are prison escapees. January 31 Allan Sheffield hijacks a DC-8 from San Francisco to Cuba; he says he is "tired of TV dinners and tired of seeing people starve in the world". February 3 A 21-year-old student and his girlfriend attempt to hijack a plane from New York City to Cuba; when the pilot refuels in Miami, the hijackers allow the passengers to deplane; the police capture the hijackers. February 3 Two Cubans hijack a 727 from Newark, New Jersey, to Cuba. Candid Camera creator Allen Funt was a passenger on the flight, and because other passengers recognized him, they assumed and believed that the hijacking was a stunt for the show, despite his protestations. Funt and others were later released after 11 hours of being held captive. February 10 A man born in Cuba hijacks a DC-8 from Atlanta to Cuba. February 25 A man hijacks a DC-8 from Atlanta to Cuba; he surrenders to U.S. authorities in Prague, CSR, in September 1969; he is sentenced to life imprisonment on July 7, 1970.